Thirty Years of Adventure, Community, and the Lifelong Mission Behind Trail Head Cyclery, Cupertino, California
MTB Girls Magazine had the exclusive opportunity to sit down with Lars Thomsen, founder of Trail Head Cyclery in Cupertino, California, for an in-depth conversation about his journey, the evolution of the shop, and the community that has grown around it over the past three decades. From a father’s unexpected dream to becoming a cornerstone of the mountain bike community, Lars shares the story behind Trail Head Cyclery, the lessons learned along the way, and the passion that continues to drive him forward.
Here’s what we discovered!
“Did you like the questions?” I ask Lars Thomsen as we begin our conversation at Trail Head Cyclery.
“I do. I love these questions,” he says.
I tell him I wanted this interview to start with power — to pedal hard into the beginning — because this is more than the story of a bike shop. This is the founder’s story.
And he is right.
The story of Trail Head Cyclery is a story about family, community, adventure, and a lifelong commitment to mountain biking. As the shop prepares to celebrate its 30th anniversary on April 20, 2027, Lars reflects on the unexpected journey that began with his father’s dream and became a lasting part of the mountain bike community.
For three decades, Trail Head Cyclery has remained an independent bike shop in an industry that has changed dramatically. Its success has never been only about selling bikes, it has always been about helping people discover the freedom, confidence, and connection that comes from riding.
The Founder Story Begins
The story starts in Santa Barbara, California, where Lars was attending the University of California, Santa Barbara, earning degrees in geography and geology. His career path was focused on water quality and environmental science, while mountain biking was simply the passion that shaped his everyday life.
“I was riding my mountain bike like a fiend,” Lars recalls. “I was an avid mountain biker my whole life.”
Opening a bike shop was never part of the original plan. Working at bike shops helped him support himself through college, but riding was what truly connected him to the sport.
“I didn’t have a car because biking was more efficient,” he says. “Mountain biking was just something I was really passionate about.”
That passion eventually inspired someone unexpected: his father, John Thomsen.
A Father’s Dream and a Son’s Passion
John Thomsen had already lived several careers. He was a musician, a teacher, and later a successful real estate entrepreneur. When Lars introduced him to mountain biking, John saw something powerful in the sport.
“He got into it because he saw the joy it brought me,” Lars explains.
John recognized that mountain biking was more than recreation. It created adventure, community, and connection. Eventually, he surprised Lars with an idea: he wanted to retire by opening a bike shop.
Lars wasn’t convinced.
“I was like, ‘No one’s ever made any money doing that, Dad. Stop.’”
But John had a vision. And Lars realized that if his father was going to chase this dream, he wanted to be part of the journey.
Together, they created Trail Head Cyclery.
Building Trail Head Cyclery
The name was developed in 1996, and the doors officially opened in 1997 at Cambrian Park Plaza near Los Gatos, California. The location was intentional — positioned between major highways and the gateway to the Santa Cruz Mountains. It was a place where riders could stop on their way to the trails or after a day of adventure. The space itself needed imagination. The future bike shop had previously been a pet store, but Lars and John saw potential.
“We were scavenging metal and wood to create our own fixtures,” Lars says. “We were just being creative.”
That creativity became part of the shop’s identity. Trail Head Cyclery reflected the culture of mountain biking itself: authentic, resourceful, adventurous, and connected to the outdoors.
Beyond a Bike Shop
From the beginning, Lars believed a bike shop should do more than sell products. It should create riders, build confidence, and bring people together.
That philosophy led Trail Head Cyclery to become an early leader in consumer mountain bike demo events. In the 1990s, demos were primarily designed for industry insiders, but Lars believed everyday riders deserved the opportunity to experience bikes before making a decision.
“I didn’t want to sell people mountain bikes I hadn’t ridden,” he says.
In 1999, Lars and Specialized representative Steve Heaton hosted the first Trail Head Cyclery dirt demo event at Santa Teresa County Park.
“We had maybe 12 or 14 people take bikes out over the weekend,” Lars recalls. “We were high-fiving. We were so stoked.”
That simple idea helped shape a culture that continues throughout mountain biking today.
Creating Community Through Riding
Trail Head Cyclery’s impact has always extended beyond the walls of the shop. Lars has spent decades supporting youth programs, events, trail advocacy, and opportunities that help more people find their place in mountain biking.
“One of our superpowers is bringing youth into the sport,” he says.
For Lars, riding creates much more than technical skills. It builds confidence, leadership, and belonging.
He has also focused on helping new riders — especially those who may feel intimidated when entering the sport — find a welcoming path into mountain biking.
“We want people to go from fear to fun as quickly as possible,” Lars says.
Through events like the annual MTB Getaway at Wente Scout Reservation, Trail Head Cyclery creates spaces where riders can disconnect, explore, and build community.
“It’s not a resort,” Lars explains. “It’s rugged, natural, and removed from the concrete jungle.”
A Voice for Trails
Lars’s influence reaches far beyond retail. He has spent years advocating for trail access and sustainable mountain biking, working alongside land managers and the riding community.
Trail Head Cyclery helped support the development of the Soquel Demonstration State Forest Flow Trail, including sponsorship of Segment Six.
“People have no idea how hard it is to build trail,” Lars says.
His role has often been connecting riders with the people responsible for protecting and managing public lands.
“I feel like a conduit,” he explains. “I’m connecting the needs of the riders with the people managing the land.”
The Captain of Trail Head
As Trail Head Cyclery approaches 30 years, Lars continues to look forward rather than backward.
The shop’s anniversary will be a celebration of the people, riders, and community members who helped shape its journey. But for Lars, the mission remains the same: keep learning, keep adapting, and keep building connections through bicycles.
That is why The Captain of Trail Head is such a fitting title.
His story has always been about exploration — from discovering mountain biking as a young rider, to navigating unknown trails, to building a bike shop that became a community institution.
When asked what keeps him inspired after three decades, Lars answers simply:
“Constantly evolving. Constantly learning. Constantly navigating the world of mountain biking.”
A sailor. A mountain biker. A community builder. The Captain of Trail Head. And the journey is far from over.
Keep climbing. Keep exploring. Keep riding.
